The Problem with To-Do Lists

to-do lists

There is no shortage of blogs and resources on how to effectively manage our time, however there is a problem with the tools that are available to us. To-do lists and calendars are both restrictive, each in their own way.

The problem with flat to-do lists

Keeping a to-do list is a great way of taking the individual items off your mind to allow you to focus on the task at hand. However, problems arise when your list grows overwhelmingly long. No one wants to scan a long list of tasks, before they choose what to work on. Not only is a long to-do list de-motivating, but picking a single item to work on creates a sense of opportunity cost. No matter what you choose you will be left feeling “Is this the optimal use of my time?”

Have you ever wondered why when you have too much on your to-do list you end up checking your email every few minutes, or surfing the web instead of working on your tasks? Psychologist Barry Schwartz explored the effects of having too many choices on our well-being. Schwartz found that when people are faced with having to choose one option out of many desirable choices, they will begin to consider hypothetical trade-offs. Their options are evaluated in terms of missed opportunities instead of the opportunity’s potential. This increases our negative emotions. He argues that eliminating choices can greatly reduce anxiety.

The problem with number ratings

Too often to-do lists try to solve the problem of prioritization with a priority number system. Something like 1 for high priority, 2 for medium and 3 for low. The problem is that high or medium doesn’t mean anything unless you define it. Unfortunately, the usual attempts at such definitions is a categorical description. e.g. high for a task with major impact. In reality this only shifts the ambiguity by one layer, because terms like major and minor are just as subjective as high and medium. In my experience, number ratings end up being a waste of time. When such systems are deployed, all tasks eventually get assigned a number 1.

The problem with calendars

Daniel Markovitz wrote an interesting post explaining the problem with to-do lists. He suggests “living in your calendar” as an alternative. This way you can look at your calendar and immediately find out what you need to work on next. There is no choice of tasks. The obvious downside of this method is the large overhead of putting every single task in a specific calendar spot. We need a speedier approach! Something easy to stick to.

In addition to the large overhead flaw, calendars solve the problem of too much choice by offering no choice. It is on the other extreme of the choice scale. Forcing rigidity and inflexibility into an otherwise flexible schedule will only set us up for failure. If your creative juices are flowing, wouldn’t it be a waste to work on something mechanical just because it’s what you put in your calendar?

The solution – Give yourself just the right amount of choice

The solution is to break down your long to-do list into flexible milestones. The milestones can be weekly, monthly or anything else that fits. Think of it as a marriage between a to-do list and a calendar—splitting a long to-do list into small manageable chunks. This allows for greater flexibility than “living in your calendar”, while keeping your choices limited. How is this method superior?

1. Ease of planning

Splitting your tasks into rough time-frames adds less planning overhead than giving each task an exact slot in the calendar. You only need to decide roughly when you want to get a certain task done. It’s enough to say I’ll put it in for next week.

2. Agility

You can more easily shuffle things around as you go. Unexpected things happen, and being able to handle the situation and quickly re-prioritize your work is invaluable to getting things done. Quickly adapting your schedule is an invaluable skill to acquire.

3. Give your milestones context…

… when you can. Working towards incremental goals is motivating and allows you to celebrate your incremental successes along the way. If you can split your milestones in such a way that each milestone represents a goal, go for it. For example, if you’re working on a website, one milestone can include all the tasks you need to do before the first launch of your site. If you’re writing a book, it can be the first chapter of the book. If you’re working on a project for a customer, it can be all the tasks you need to do before your next meeting with the customer… and so on. To keep your schedule flexible and keep room for the unexpected, you can vary the milestone length as needed.

4. The right amount of choice

When it comes to choosing your next task, you only need to look at your current milestone. It’ll give you a good range of alternatives, yet not too many to lead to a decision-making paralysis.

Please tell us your thoughts about to-do lists and other task management tools in the comments below!

Photo by robstephaustralia.

Nada Aldahleh is the Co-Founder of Sandglaz, an online task management application for individuals and teams. She is an entrepreneur and a software developer living in Toronto, Canada.


  1. Cas Mollien on the 11th April

    Nice article. I have personally been using CheckVist for several years, because if offers the flexibility and functionality I need, without the clutter.

    For me, there is an important distinction that I make when using lists. There is the todo list, and the checklist. These are two completely different things with different purposes, and they work side-by-side.

    The todo list, by definition, collects things that I have to do at some point, but not necessarily today. They may be priorities, but they are more global (asap, soon, whenever).

    The checklist is a non-negotiable list of, mostly small, tasks that must be done each day. One of the first items on the checklist is to go over the todo list and select the 3 tasks that can be done today, that yield the most results and add them to the checklist.

    Everything on the checklist is actionable and can be done in no more than 15 minutes. Larger items get broken up into steps that take 5-15 minutes to complete, so it is easy to check things off and complete the daily tasks as well as the 3 most yielding tasks for the day.

    Because if the 5-15 minute item timeframe, I can easily re-arrange tasks without loosing track of what I am doing. And, depending on what I am working on, it allows me to schedule my day to 80% full, leaving 20% for ‘interruptions and unplanned’ items, or do exactly the opposite. When I have time left in the day, I just pick up on some of the items of the todo list.

    This way, I know that I get done what I need to get done, while maintaining a balance. And, it forces me to take a very critical view on the tasks that I assign myself…

    • Nada Aldahleh on the 26th April

      Sounds like you have the right attitude towards your to-do’s; the 80%-20% and allowing yourself to re-arrange as you need, or pick up to-do’s when you have time left. It’s also important that it doesn’t take too long to maintain 🙂

  2. alanc230 on the 11th April

    When you’re spending more time making and prioritizing your to-do list than actually working on the tasks, that’s when you know you need to rethink your strategy.

  3. Rohit Khare on the 11th April

    I agree that To-Do lists become long and the creator looses interest soon. But it all depends on how the list is created.

    I personally maintain a diary with my To-Do list. I include only those things that require my immediate attention and none of the things that can be done tomorrow as well.

    As Franklin Covey says: First Things First.

    While creating To-Do lists, people are over ambitious at the start and loose interest as nothing gets completed. This is because we are too busy trying to complete those things that need not be done today.

    • Nada Aldahleh on the 26th April

      It’s a good point 🙂

      Though sometimes we write things down just so that we don’t forget them, even if we don’t plan to do them until next week or even later. In these situations it’s useful to jot them down in rough time-frames.

      That’s what the infinity grids are for:

  4. Peter on the 11th April

    For me, to-do lists work best when I prepare them the day before – that way I mentally prepare for the tasks and I can start being productive right away.

    Also you shouldn’t underestimate the motivational boost from striking through the tasks on paper, that’s why I’ve always liked to note down my tasks on paper…although I usually use Asana now because there are so many tasks.

    I also suggest to set precise – and realistic – time limits for each task. You’ll notice that you’ll almost always need exactly the amount of time you’ve applied to a task before!

    • Nada Aldahleh on the 26th April

      It works for me too. The day before or the milestone before (which could be ~1 week long) I prepare what I plan to work on next. I drag and drop from the Later column or future milestones to the current one.

  5. Glenn on the 15th April

    I’ve been using prioritized to do lists in spiral 7 X 9 1/2 ” notebooks for over 20 years now and it works quite well. Tasks are numbered but prioritized in the left hand margin by A, B, C, etc. — many times with several As, several Bs, etc. Since I try to drive myself by committing to deadlines (either with a client or in some other ‘public’ way) the top priorities usually relate to deadlines.

    If I hit a sticky spot (‘latency’) that is usually a red flag to rewrite the list — strip out the things that have become unimportant and re-prioritize the rest. The other key to keep moving forward is to always have 2 to 3 things on your list which you are committed to finishing today.

    Paper notebooks never crash or take a long time to boot.

    What the method lacks is contextualizing the tasks within projects. I generally have 1 to 3 high priority projects and 3 to 5 lower priority projects going all the time. Sometimes an entire project needs to be placed on either the front or the back burner. It would be nice to be able to “drag & drop” a project off of the current to do list and onto the next “layer down” on my imaginary stack of lists.

  6. HP van Duuren on the 20th April

    Thanks for your post Nada Aldahleh,

    I prefer to work with a Have Done list,

    As you can see in a post titled:

    Because that way it feels more Motivating when you see you have actually completed things. It also will make it easier to see what else you could Improve or Complete and makes it easier to spot the things that really matter.

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